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p-Aminoacetophenone → N-[4-(1-hydroxyiminoethyl)phenyl]-N'-(1-methoxycarbonyl-2-carbamoylethyl)urea

HRID 649691
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 649691
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=O.[N-:11]=[C:12]=[O:13].[CH3:14][O:15][C:16](=[O:23])[C@H:17]([CH2:19][C:20](=[O:22])[NH2:21])N.Cl.[NH2:25][OH:26].C(OC)(OC)OC>C1COCC1.N1C=CC=CC=1>[OH:26][N:25]=[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:12]([NH:11][CH:17]([C:16]([O:15][CH3:14])=[O:23])[CH2:19][C:20](=[O:22])[NH2:21])=[O:13])=[CH:6][CH:5]=1)[CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7468p-AminoacetophenoneHCID 9005Trimethyl orthoformateHCID 443297Hydroxyamine hydrochlorideHCID 86741878Asparagine methyl ester isocyanate

Produkt 1

HCID 86741883N-[4-(1-hydroxyiminoethyl)phenyl]-N'-(1-methoxycarbonyl-2-carbamoylethyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049
Pyridine
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 2.7 g 4-aminoacetophenone in 40 mL is THF added dropwise to a solution of 0.02 mol of asparagine methyl ester isocyanate and 5 mL pyridine in 40 mL THF, and the reaction mixture is stirred for 3 hours. The solvent is then removed by rotary evaporator. The residue is dispersed in 50 mL CH3OH, and 0.022 mol hydroxylamine hydrochloride and 0.06 mol trimethyl orthoformate are added. The reaction mixture is heated to reflux for 10 hours. The solvent is removed by rotary evaporator. Addition of water to the residue results in precipitation of N-[4-(1-hydroxyiminoethyl)phenyl]-N'-(1-methoxycarbonyl-2-carbamoylethyl)urea, which is isolated by filtration and dried.

Aufarbeitung

  1. customThe solvent is then removed by rotary evaporator
  2. additionThe residue is dispersed in 50 mL CH3OH
  3. temperatureThe reaction mixture is heated
  4. temperatureto reflux for 10 hours
  5. customThe solvent is removed by rotary evaporator
  6. additionAddition of water to the residue

Quellen und Nachweise

ORD-Eintrag
ord-9dafeabf17cf4a7b821cdcf6e393a8d2
Quelldatensatz
uspto-grants-1988_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04740611

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